EP3914677A2 - Esters d'estolide et leur utilisation comme huile de base dans les lubrifiants - Google Patents

Esters d'estolide et leur utilisation comme huile de base dans les lubrifiants

Info

Publication number
EP3914677A2
EP3914677A2 EP20700952.3A EP20700952A EP3914677A2 EP 3914677 A2 EP3914677 A2 EP 3914677A2 EP 20700952 A EP20700952 A EP 20700952A EP 3914677 A2 EP3914677 A2 EP 3914677A2
Authority
EP
European Patent Office
Prior art keywords
acid
acids
carbon atoms
hydroxycarboxylic acids
monoalcohols
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP20700952.3A
Other languages
German (de)
English (en)
Inventor
Wilhelm Huber
Hermann Josef Stolz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Peter Greven & Co KG GmbH
Original Assignee
Peter Greven & Co KG GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Peter Greven & Co KG GmbH filed Critical Peter Greven & Co KG GmbH
Publication of EP3914677A2 publication Critical patent/EP3914677A2/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/301—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/66—Hydrolytic stability

Definitions

  • Estolide esters and their use as a base oil in lubricants are also useful as a base oil in lubricants.
  • the present invention relates to estolide esters, their production and use as base oils for lubricants and these lubricants.
  • Synthetic esters have been used as base fluids or additives for lubricants for decades.
  • the driving force behind this development was initially the concern about the finite nature of the crude oil reserves.
  • thoughts about toxicity and biodegradability also played an increasingly important role.
  • the aspect of sustainability is becoming increasingly important.
  • closed material cycles from renewable raw materials should be used.
  • a balanced C02 balance is one of the decisive factors.
  • Lubricants are said to reduce the friction between moving surfaces. This significantly reduces wear between the workpieces and prevents excessive heat build-up. To cool the lubricants the surface and ensure that particles are removed.
  • esters have a number of advantages over mineral oils. Due to the polarity of the ester group, they have a high affinity for metal surfaces. This results in good lubricating properties. They have a lower volatility than mineral oils and a high viscosity index, which means that the viscosity is less dependent on the temperature. Esterification with dicarboxylic acids allows the viscosity values of the esters to be varied within a wide range. However, esters also have disadvantages. Oxidation stability and thermal stability are not always sufficient for critical applications, especially with some unsaturated esters.
  • the saponification is carried out in a mineral oil and then filled up with ester oil, or else finished metal soaps are used.
  • ester oil or else finished metal soaps are used.
  • Other thickeners, such as polyurea, can also be used.
  • Hydroxycarboxylic acids include unsaturated hydroxycarboxylic acids with a)
  • estolide esters according to the invention are thus obtainable by esterifying hydroxy acids with one another. This creates oligomers or polymeric esters.
  • the reaction mixture also contains either monocarboxylic acids or monoalcohols. These serve as 'capping agents' because they prevent further oligomerization or polymerization.
  • polyols with at least two hydroxyl groups or carboxylic acids with at least two carboxy groups are used. These serve for further crosslinking in order to increase the degree of oligomerization or polymerization. These connections are also called composite agents.
  • monocarboxylic acids having 6 to 22 carbon atoms and monoalcohols are used together and thus serve as capping agents.
  • unsaturated hydroxycarboxylic acids are used as hydroxycarboxylic acids. It is also possible to use additionally saturated hydroxycarboxylic acids. Hydroxycarboxylic acids are carboxylic acids that carry at least one hydroxyl group, but they can also carry several hydroxyl groups.
  • Preferred lengths of the hydroxycarboxylic acids are 12 to 18 or 12 to 20 carbon atoms. They can be branched or unbranched. Preferred examples of such unsaturated hydroxycarboxylic acids are ricinoleic acid, lesquerolic acid, 15-hydroxy-linoleic acid, auricolic acid or hydroxypalmitoleic acid and mixtures thereof. Ricinoleic acid is particularly preferred.
  • the proportion of unsaturated hydroxycarboxylic acids in the hydroxycarboxylic acids is preferably 10% by weight, more preferably at least 25% by weight or at least 50% by weight or at least 80% by weight or at least 99% by weight.
  • saturated fatty acids e.g. hydrogenated ricinoleic acid, hydroxypalmitic acid or hydroxydodecanoic acid or mixtures thereof.
  • monocarboxylic acids having 6 to 22 carbon atoms, preferably 6 to 18 carbon atoms, are used as the second constituent.
  • monocarboxylic acids are hexanoic acid, caprylic acid, capric acid, pelargonic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid and behenic acid or mixtures thereof.
  • branched monocarboxylic acids are in particular isostearic acids and monomer acids.
  • Monomer acids are a by-product of the production of dimer fatty acids. Dimer fatty acids are made from different fatty acids by means of boiling. A fatty acid with conjugated double bonds (conjugic acid) and other unsaturated fatty acids are necessary.
  • fatty acids are conjugated linoleic acids.
  • the reaction takes place by means of Diels-Alder addition, which forms a partially unsaturated C6 ring.
  • trimers and monomers of the fatty acids can also be present in a mixture.
  • Monomer acids are separated from the reaction mixture by distillation.
  • Polyols are used as the third component.
  • the polyols are compounds which carry at least two hydroxyl groups. In contrast to the hydroxycarboxylic acids, they must not have a carboxylic acid function.
  • the polyols preferably contain no ⁇ -H atoms.
  • polyols are trimethylolpropane, di-trimethylolpropane, neopentyl glycol, pentaerythritol, dipentaerytrithol, monoethylene glycol (1,2 ethanediol) and mixtures thereof.
  • monoalcohols having 8 to 18 carbon atoms are used as the second component.
  • Particularly suitable monoalcohols are: a) octanol, decanol, isotridecyl alcohol, and mixtures thereof.
  • Polyvalent carboxylic acids that is to say carboxylic acids with at least two carboxy groups, are then used as the third component. In contrast to the hydroxycarboxylic acids, they must not have a hydroxy function
  • 1,4-butanedioic acid succinic acid
  • 1,6-hexanedioic acid adipic acid
  • Nonanedioic acid azelaic acid
  • 1,10-decanedioic acid sebacic acid
  • the monocarboxylic acids or monoalcohols (capping agents) are branched or at least branched compounds are contained in a mixture.
  • the carboxylic acids are branched with at least two carboxy groups or polyols (compounding agents) or at least branched compounds are contained in a mixture.
  • both compounding agents and capping agents are branched or at least branched compounds are contained in a mixture.
  • a range from 3: 1 to 1: 1 has proven to be suitable.
  • a molar ratio of hydroxycarboxylic acids to polyols has proven to be a ratio of 12: 1 to 2: 1, preferably 7: 1 to 2: 1.
  • the estolide esters according to the invention typically have a viscosity of at least 80 mm 2 / s at 40 ° C. If only monoalcohols and monoacids according to variant c) are used, the estolide esters according to the invention typically have a viscosity of at least 40 mm 2 / s at 40 ° C.
  • the invention also relates to a process for the preparation of the estolide esters according to the invention, comprising the steps of esterifying
  • hydroxycarboxylic acids with 12-24 carbon atoms, the hydroxycarboxylic acids comprising unsaturated hydroxycarboxylic acids
  • estolide esters according to the invention as a base oil for lubricants and a lubricant containing an estolide ester according to the invention.
  • Such lubricants preferably contain further additives selected from the group of antioxidants, defoamers, extreme pressure additives, wear inhibitors and pour point depressants.
  • Reaction mixture is ⁇ 30 mg KOH / g.
  • the mixture is cooled and 285.9 g of isotridecyl alcohol and 0.1 g of SnO are added as a catalyst.
  • the product is then esterified at 180-220 ° C and 10-100 mbar until the acid number is ⁇ 2 mg KOH / g. After removing the catalyst, an ester with a viscosity of approx. 46 mm 2 / s is obtained.
  • Reaction mixture is ⁇ 30 mg KOH / g.
  • the mixture is cooled and 66.8 g of TMP and 0.1 g of SnO are added as a catalyst.
  • the product is then esterified at 180-220 ° C and 10-100 mbar until the acid number Is ⁇ 2 mg KOH / g. After removing the catalyst, an ester with a viscosity of about 225 mm 2 / s is obtained.
  • the hydrolysis stability of the estolides was determined in accordance with ASTM D 2619. The difference in the acid number before and after the test was used as the measurement variable. The values of the estolides according to Examples 1-3 were compared with complex esters of the respective ISO VG class.
  • estolides according to the invention were compared.
  • the values of the estolides according to Examples 1-3 were compared with complex esters of the respective ISO VG class.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne des esters d'estolide obtenus par estérification - d'acides hydroxycarboxyliques comportant 12 à 24 atomes de carbone, les acides hydroxycarboxyliques comprenant des acides hydroxycarboxyliques insaturés avec a) - des acides monocarboxyliques comportant 6 à 22 atomes de carbone et - des polyols comportant au moins deux groupes hydroxyle ou b) - des monoalcools comportant 8 à 22 atomes de carbone et - des acides carboxyliques linéaires comportant au moins deux groupes carboxyle ou c) - des acides monocarboxyliques comportant 6 à 22 atomes de carbone et - des monoalcools comportant 8 à 22 atomes de carbone.
EP20700952.3A 2019-01-23 2020-01-23 Esters d'estolide et leur utilisation comme huile de base dans les lubrifiants Pending EP3914677A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP19153186 2019-01-23
PCT/EP2020/051661 WO2020152286A2 (fr) 2019-01-23 2020-01-23 Esters d'estolide et leur utilisation comme huile de base dans les lubrifiants

Publications (1)

Publication Number Publication Date
EP3914677A2 true EP3914677A2 (fr) 2021-12-01

Family

ID=65200699

Family Applications (1)

Application Number Title Priority Date Filing Date
EP20700952.3A Pending EP3914677A2 (fr) 2019-01-23 2020-01-23 Esters d'estolide et leur utilisation comme huile de base dans les lubrifiants

Country Status (6)

Country Link
US (1) US11591535B2 (fr)
EP (1) EP3914677A2 (fr)
JP (1) JP2022518576A (fr)
KR (1) KR20210119400A (fr)
AU (1) AU2020211346A1 (fr)
WO (1) WO2020152286A2 (fr)

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5458795A (en) * 1994-01-28 1995-10-17 The Lubrizol Corporation Oils thickened with estolides of hydroxy-containing triglycerides
JPH07228881A (ja) 1994-02-17 1995-08-29 Ito Seiyu Kk エステル組成物
WO2009139003A1 (fr) * 2008-05-14 2009-11-19 Council Of Scientific & Industrial Research (An Indian Registered Body Incorporated Under The Registration Of Societies Act (Act Xxxi Of 1860) Esters d'estolides à base d'acides gras d'huile de ricin et leurs dérivés, pouvant servir de support pour lubrifiants
WO2011037778A1 (fr) * 2009-09-24 2011-03-31 Dow Global Technologies Inc. Compositions à base d'estolides présentant de remarquables propriétés à basse température
EP2611891A1 (fr) * 2010-08-31 2013-07-10 Biosynthetic Technologies, LLC Procédés catalytiques de préparation d'huiles de base comprenant des étholides
EP2619291A1 (fr) * 2010-09-24 2013-07-31 Dow Global Technologies LLC Dérivés d'étholide préparés à partir de triglycérides
WO2012173671A1 (fr) * 2011-06-17 2012-12-20 Lubrigreen Biosynthetics, Llc Compositions comprenant des composés estolide et leurs procédés de préparation et d'utilisation
AU2012271126B2 (en) * 2011-06-17 2016-10-13 Biosynthetic Technologies, Llc Estolide compositions exhibiting high oxidative stability
US8829216B2 (en) * 2011-08-31 2014-09-09 Biosynthetic Technologies, Llc Hydroxy estolides, poly-capped estolides, and methods of making the same
EP2794824B1 (fr) * 2011-12-19 2018-10-31 Biosynthetic Technologies, LLC Procédés de préparation d'huiles de base d'estolide et composés oligomères qui comprennent une métathèse croisée
US9018406B2 (en) * 2012-03-27 2015-04-28 Biosynthetic Technologies, Llc Dicarboxylate-capped estolide compounds and methods of making and using the same
WO2013184255A1 (fr) * 2012-06-04 2013-12-12 Biosynthetic Technologies, Llc Procédés de préparation d'huiles de base et de lubrifiants de type estolides faisant appel à la transestérification
EP3019465A1 (fr) * 2013-07-09 2016-05-18 Biosynthetic Technologies, LLC Estolides de polyol et procédés de fabrication et d'utilisation correspondants
WO2015047903A1 (fr) * 2013-09-25 2015-04-02 Biosynthetic Technologies, Llc Lubrifiants pour moteurs à deux temps comprenant des composés estolide
JP6463741B2 (ja) * 2013-10-02 2019-02-06 バイオシンセティック テクノロジーズ，リミティド ライアビリティ カンパニー 潤滑剤組成物において優秀な性質を示すエストリド組成物
EP3325582A1 (fr) * 2015-07-24 2018-05-30 Evonik Oil Additives GmbH Utilisation d'esters de polyclycérine en tant que modificateurs de frottement dans des formulations de lubrifiants
US20170152209A1 (en) * 2015-11-30 2017-06-01 Biosynthetic Technologies, Llc. Ultra high-viscosity estolide base oils and method of making the same
AU2017355295C1 (en) * 2016-11-04 2021-08-12 Indorama Ventures Oxides Llc Estolides of vegetable oil alkoxylates and methods of making and using
DE102018002041A1 (de) * 2017-03-29 2018-10-04 Klüber Lubrication München Se & Co. Kg Neue Esterverbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE102018002891A1 (de) * 2017-04-13 2018-10-18 Klüber Lubrication München Se & Co. Kg Neue Esterverbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung
JP6518815B1 (ja) * 2018-05-01 2019-05-22 第三化成株式会社 エステル化合物および潤滑油基油
US11104859B2 (en) * 2019-08-12 2021-08-31 The United States Of America, As Represented By The Secretary Of Agriculture Polyethylene diester viscosity modifiers
US20210115352A1 (en) * 2019-10-22 2021-04-22 University Of North Texas Lubricant compositions having enhanced estolide content, methods of making, and uses thereof

Also Published As

Publication number Publication date
KR20210119400A (ko) 2021-10-05
JP2022518576A (ja) 2022-03-15
US20220112439A1 (en) 2022-04-14
AU2020211346A1 (en) 2021-08-12
US11591535B2 (en) 2023-02-28
WO2020152286A2 (fr) 2020-07-30
WO2020152286A3 (fr) 2020-10-01

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